Nitratoethyl-5H-tetrazoles: improving the oxygen balance through application of organic nitrates in energetic coordination compounds

Abstract

1- and 2-Nitratoethyl-5H-tetrazole (1-NET, 2-NET) were prepared through nitration of the respective alkyl alcohol using 100% nitric acid. A mixture of 1- and 2-hydroxyethyl-5H-tetrazole was obtained after alkylation of 1,5H-tetrazole....

Tuning the Properties of 5‐Azido and 5‐Nitramino‐tetrazoles by Diverse Functionalization – General Concepts for Future Energetic Materials

“…The room temperature density of nitratoethyl compound 10 is clearly superior to that of the azidoethyl derivative (1.519 g cm −3 for 7 , 1.638 g cm −3 for 10 ). This trend has also been observed in previous studies [20] , since the nitratoethyl unit offers more possibilities for intermolecular interactions on the one hand and contains more and heavier atoms on the other, which also arrange themselves better in space. Since there are no good opportunities for intermolecular interactions for the present nonpolar residues, the three‐dimensional structure of 7 is mainly based on the fact that the azido and azidoethyl substituents avoid each other with a as large spatial distance as possible in order to counteract possible destabilizing interaction (Figure 6 B)).…”

Engineering bistetrazoles: (E)-5,5′-(ethene-1,2-diyl)bis(1H-tetrazol-1-ol) as a new planar high-energy-density material

“…Compound 8 crystallizes in the triclinic space group P% 1 with one chemical formula unit per unit cell (Fig. (5)). The calculated crystal density for compound 8 is 1.585 g cm À3 at 100 K. Relative to compound 7, compound 8 exhibits higher density due to the planar bistetrazole anions.…”

“…[1][2][3] The tetrazole ring allows facile attachment of a variety of groups to the carbon atom at the five position and substitution on nitrogen at the N1 and N3 positions. [4][5][6][7][8] Over the past decades, many linked or bridged tetrazole derivatives have been developed through the rational combination of tetrazole and substituents such as NQN-, -NH-, -C(O)-, -C-C-, and azole rings. [9][10][11][12][13][14][15] The physicochemical properties of linked-tetrazole derivatives can be easily altered by modifying the linking group.…”

“…34 Attempts to design conjugated planar HEDMs have been made by many researchers. For example, fused tetrazolo 1,2,4,5-tetrazine N-oxides, 4-amino-3,7-dinitro-[1,2,4]triazolo[5,1-c][1,2,4]triazine, and nitroamino-functionalized 1,2,4triazolo [4,3-b] [1,2,4,5]tetrazine are planar conjugated structures reported as high-performance materials. [35][36][37] Recently it was demonstrated that tetrazole or triazole ring substituted FOX-7like molecules exhibit good thermal stability and improved sensitivity due to the planar conjugated structures.…”

“…[38][39][40] Inspired by the good performance of conjugated planar energetic compounds, we speculated that the introduction of a planar conjugated ethene link between tetrazole rings would improve the density, heat of formation and insensitivity. Now we have synthesized ethane and ethene linked bistetrazole derivatives: 1,2-di(1H-tetrazol-5-yl)ethane ( 4), (E)-1,2-di(1H-tetrazol-5yl)ethene (5), and the ethene-linked bis(1H-tetrazol-1-ol) derivative, (E)-5,5 0 -(ethene-1,2-diyl)bis(1H-tetrazol-1-ol), (6) using readily available starting materials. Dihydroxylammonium salts 7, 8 and 9 are obtained by reacting two equivalents of hydroxylamine (50% in water) with compounds 4, 5 and 6.…”